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Hydrogen bond-assisted 1,2-cis o-glycosylation under mild hydrogenolytic conditions

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Chinese Chemical Letters 2023年第4期34卷 313-317页

作者： Gefei Li Yanlong Luo Juan Mo Masato Noguchi Jie Jing Zhenyang Luo Shin-ichiro Shoda Xin-Shan Ye College of Science Nanjing Forestry UniversityNanjing 210037China State Key Laboratory of Natural and Biomimetic Drugs School of Pharmaceutical SciencesPeking UniversityBeijing 100191China Department of Biomolecular Engineering Graduate School of EngineeringTohoku UniversitySendai 980-8579Japan

A hydrogen bond-assisted α-selective glycosylation reaction by using 4,6-dibenzyloxy-1,3,5-triazin-2-yl(DBT) β-glycosyl donors was developed for the efficient construction of 1,2-cis-α-glycosidic bond in natural products. This method was applied successfully to the direct synthesis of complex oligosaccharidederived glycolipids with simple protecting chemistry. Mechanistic studies using the NMR spectroscopy and DFT calculation provide a proof of concept for hydrogen bond-assisted glycosylation reaction towardsα-specific construction of o-glycosidic linkage.

关键词： o-glycosylation Hydrogen bond α-Selectivity Glycolipid Natural product

oGP: A Repository of Experimentally Characterized o-glycoproteins to Facilitate Studies on o-glycosylation

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Genomics, Proteomics & Bioinformatics 2021年第4期19卷 611-618页

作者： Jiangming Huang Mengxi Wu Yang Zhang Siyuan Kong Mingqi Liu Biyun Jiang Pengyuan Yang Weiqian Cao Department of Chemistry and Institutes of Biomedical Sciences Fudan UniversityShanghai 200032China The Fifth People’s Hospital Fudan Universityand the Shanghai Key Laboratory of Medical Epigeneticsthe International Co-laboratory of Medical Epigenetics and MetabolismMinistry of Science and TechnologyFudan UniversityShanghai 200032China NHC Key Laboratory of Glycoconjugates Research(Fudan University) Shanghai 200032China

Numerous studies on cancers, biopharmaceuticals, and clinical trials have necessitated comprehensive and precise analysis of protein o-glycosylation. However, the lack of updated and convenient databases deters the storage of and reference to emerging o-glycoprotein data. To resolve this issue, an o-glycoprotein repository named oGP was established in this *** was constructed with a collection of o-glycoprotein data from different sources. oGP contains 9354 o-glycosylation sites and 11,633 site-specific o-glycans mapping to 2133 o-glycoproteins, and it is the largest o-glycoprotein repository thus *** on the recorded o-glycosylation sites, an o-glycosylation site prediction tool was developed. Moreover, an oGP-based website is already available(http://***/). The website comprises four specially designed and user-friendly modules:statistical analysis, database search, site prediction, and data submission. The first version of oGP repository and the website allow users to obtain various o-glycoprotein-related information, such as protein accession Nos., o-glycosylation sites,o-glycopeptide sequences, site-specific o-glycan structures, experimental methods, and potential o-glycosylation sites.o-glycosylation data mining can be performed efficiently on this website, which will greatly facilitate related studies. In addition, the database is accessible from oGP website(http://***/***).

关键词： o-glycosylation o-glycoprotein repository Site prediction o-glycoprotein related website Data mining

o-glycosylation in liver cancer:Clinical associations and potential mechanisms

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Liver Research 2017年第4期1卷 193-196页

作者： Kung-Hao Liang Chau-Ting Yeh Liver Research Center Chang Gung Memorial HospitalTaoyuanTaipeiChina Medical Research Department Taipei Veterans General HospitalTaipeiChina Molecular Medicine Research Center Chang Gung UniversityTaoyuanTaipeiChina

Liver cancer can be an aggressive disease,and is highly prevalent in Asia and ***,its currently approved therapeutic strategies are far from *** progress in genomic,proteomic and glycomic profiling technologies have enabled the identification of biomarkers that significantly correlate with clinical *** biomarkers are related to o-glycosylation of glycoproteins,which belong to an important but less-explored field of liver cancer ***,we review these clinical studies and discuss potential underlying mechanisms.

关键词： o-glycosylation Post-translational modification Glycobiology Biomarkers Hepatocellular carcinoma(HCC) Glycosyltransferase

The role of intracellular protein o-glycosylation in cell adhesion and disease

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The Journal of Biomedical Research 2011年第4期25卷 227-236页

作者： Meryem Bektas David S.Rubenstein Department of Dermatology University of North Carolina-Chapel Hill School of MedicineChapel HillNorth Carolina 27599-7287USA Department of Pharmacology University of North Carolina-Chapel Hill School of MedicineChapel HillNorth Carolina 27599-7287USA Lineberger Comprehensive Cancer Center University of North Carolina-Chapel Hill School of MedicineChapel HillNorth Carolina 27599-7287USA

Post-translational protein modification, including phosphorylation, is generally quick and reversible, facilitating rapid biologic adjustments to altered cellular physiologic demands. In addition to protein phosphorylation, other post-translational modifications have been identified. Intracellular protein o-glycosylation, the addition of the simple sugar o-linked N-acetylglucosamine （o-G1cNAc） to serine/threonine residues, is a relatively recently identified post-translational modification that has added to the complexity by which protein function is regulated. Two intracellular enzymes, o-GlcNAc transferase and o-GlcNAcase, catalyze the addition and removal, respectively, of o-GlcNAc to serine and threonine side-chain hydroxyl groups. Numerous proteins, including enzymes, transcription factors, receptors and structural proteins have been shown to be modified by intracellular o-glycosylation. In this review, the mechanism and relevance of o-GlcNAc protein modification are discussed in the context of cell adhesion and several representative diseases.

关键词： o-glycosylation o-GlcNAc diabetes cancer cell adhesion

Structural insights into the sequential o-glycosylation and molecular function of serine-rich repeat proteins

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Structural insights into the sequential O-glycosylation and ...

中国生物化学与分子生物学会2016年全国学术会议

作者： Yong-Liang Jiang Yi-Hu Yang Wei-Wei Shi Hua Jin Rong-Li Zhao Yuxing Chen Cong-Zhao Zhou Hefei National Laboratory for Physical Sciences at the Microscale and School of Life Sciences University of Science and Technology of China

The serine-rich repeat proteins(SRRPs)are a large family of surface adhesins in Gram-positive *** are crucial for bacterial adhesion,immune evasion,colonization,biofilm formation and *** serine-rich repeat regions of SRRPs are usually subject to o-glycosylation for increasing the mobility and stability of nascent SRRPs.o-glycosylation is an

关键词： o-glycosylation SRRPs crystal structure glycosyltransferases

ppGalNAc-T8-mediated o-glycosylation of BMP receptor 1A suppresses breast cancer cells proliferation through up-regulating ERα expression

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ppGalNAc-T8-mediated O-glycosylation of BMP receptor 1A supp...

2020年糖科学青年科技论坛

作者： Tianmiao Huang Qiong Wu Wenli Li Yubo Liu Jianing Zhang School of Life and Pharmaceutical Sciences Dalian University of Technology

Mucin-type o-glycosylation is one of the most abundant type of o-glycosylation and plays important roles in the pathogenesis of various human carcinomas including breast cancer.A large family of polypeptide N-acetyl-α-galactosaminyltransferases（ppGalNAc-Ts） initiate and define sites of mucin-type ***,the specific mechanisms underlying ppGalNAc-Ts-mediated abnormal o-glycosylation and its roles in tumorigenesis remain poorly ***,we provided evidence that the expression of ppGalNAc-T8 was associated with breast cancer patient *** the meantime,ppGalNAc-T8 was downregulated along with reduction of estrogen receptor α（ERα） *** of ppGalNAc-T8 in breast cancer cells elevated the transcription and protein levels of ERαand suppressed colony formation suggesting an important role of ppGalNAc-T8 in cancer cells ***,knockdown of ppGalNAc-T8 leaded to the inhibition of BMP signaling,which reined ERα *** analysis suggested that BMP receptor 1 A（BMPR1 A） was o-GalNAcylated by *** analysis identified that Thr137 and Ser37/Ser39/Ser44/Thr49 of BMPR1 A were the o-glycosylation sites catalyzed by ***,we demonstrated that ppGalNAc-T8-mediated o-glycosylation of BMPR1 A played a key role in regulating the activity of BMP/SMAD/RUNX2 signaling and ERα ***,our study reveals that ppGalNAc-T8 elevated ERα expression and suppressed breast cancer cells proliferation and through modulating BMP signaling pathway.

关键词： o-glycosylation ppGalNAc-T8 BMP signaling Breast cancer

Altered o-glycosylation is associated with inherent radioresistance and malignancy of human laryngeal carcinoma

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Altered O-glycosylation is associated with inherent radiores...

2017年中国肿瘤标志物学术大会暨第十一届肿瘤标志物青...

作者： Li Shen Lu Meng Yingying Wang Qiwen Duan Li Qiu Feng Peng Zhiguo Luo Xiaoxia Dong Department of Clinical oncology Taihe HospitalHubei University of Medicine Department of biochemsitry School of Basic Medical SciencesHubei University of Medicine School of Biomedical Engineering Hubei University of Medicine Department of pharmacology School of Basic Medical SciencesHubei University of Medicine

Radioresistance(inherent or acquired) remains a major obstacle affecting theclinical outcome of radiotherapy for laryngeal carcinoma. Results from our laboratoryand other groups suggest that aberrant glycosylation contributes to cancer acquiredradioresistance. However, the role of glycosylation in inherent radioresistance oflaryngeal carcinoma has not been fully uncovered. In this study, we investigated theglycan profiling of the inherent radioresistant(Hep-2 max) and radiosensitive(Hep-2 min) cell lines using lectin microarray analysis. The results revealed that the radioresistant cell line Hep-2 max presented higher core 1 type o-glycans than the sensitive one. Further analysis of the o-glycan regulation by benzyl-α-GalNAc application in Hep-2 max cells showed partial inhibition of the o-glycan biosynthesis and increased radiosensitivity. In addition, core 1 β1, 3-galactosyltransferase(C1 GALT1) overexpression in Hep-2 min cells enhanced cell migration, invasion, and radioresistance. Conversely, knockdown of C1 GALT1 in Hep-2 max cells was able to suppress these malignant ***, mechanistic investigations showed that C1 GALT1 modified the o-glycans on integrin β1 and regulated its activity. The glycosylation-mediated radioresistance was further inhibited by anti-integrin β1 blocking antibody. Importantly, we also observed that core 1-type o-glycans expression was correlated with advanced tumor stage, metastasis,and poor survival of laryngeal carcinoma patients. These findings suggest that alteredo-glycosylation can lead to the inherent radioresistance and progression, and therefore may be important for enhancing the efficacy of radiotherapy in laryngeal carcinoma.

关键词： o-glycosylation inherent radioresistance malignancy laryngeal carcinoma

The mechanism for heavy o-glycosylation of a bacterial adhesin

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The mechanism for heavy O-glycosylation of a bacterial adhes...

中国生物化学与分子生物学会2016年全国学术会议

作者： Yong-Liang Jiang Hua Jin Rong-Li Zhao Shi-Liang Wang Hong-Bo Yang Yan-Min Ren Yuxing Chen Cong-Zhao Zhou Hefei National Laboratory for Physical Sciences at the Microscale and School of Life Sciences University of Science and Technology of China

o-glycosylation of Ser and Thr residues is an important process in all organisms,which is poorly understood due to the complex nature of known o-linked *** we analyzed the o-glycosylation profile of a mucin-like glyco... 详细信息

关键词： o-glycosylation SRRPs crystal structure glycosyltransferases

Genetic variants in C1GALT1 are associated with gastric cancer risk by influencing immune infiltration

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Journal of Biomedical Research 2024年第4期38卷 348-357页

作者： Mengfan Guo Jingyuan Liu Yujuan Zhang Jingjing Gu Junyi Xin Mulong Du Haiyan Chu Meilin Wang Hanting Liu Zhengdong Zhang Departments of Environmental Genomics and Genetic Toxicology the Key Laboratory of Modern Toxicology of Ministry of EducationCenter for Global HealthJiangsu Key Laboratory of Cancer BiomarkersPrevention and TreatmentCollaborative Innovation Center for Cancer Personalized MedicineSchool of Public Health/Institute of Clinical Researchthe Affiliated Taizhou People's Hospital of Nanjing Medical UniversityNanjing Medical UniversityNanjingJiangsu 211166China Departments of Environmental Genomics and Genetic Toxicology the Key Laboratory of Modern Toxicology of Ministry of EducationCenter for Global HealthJiangsu Key Laboratory of Cancer BiomarkersPrevention and TreatmentCollaborative Innovation Center for Cancer Personalized MedicineSchool of Public HealthNanjing Medical UniversityNanjingJiangsu 211166China Department of Bioinformatics School of Biomedical Engineering and InformaticsNanjing Medical UniversityNanjingJiangsu 211166China Department of Biostatistics Center for Global HealthSchool of Public HealthNanjing Medical UniversityNanjingJiangsu 211166China

Core 1 synthase glycoprotein-N-acetylgalactosamine 3-β-galactosyltransferase 1(C1GALT1)is known to play a critical role in the development of gastric cancer,but few studies have elucidated associations between genetic variants in C1GALT1 and gastric cancer *** using the genome-wide association study data from the database of Genotype and Phenotype(dbGAP),we evaluated such associations with a multivariable logistic regression model and identified that the rs35999583 G>C in C1GALT1 was associated with gastric cancer risk(odds ratio,0.83;95% confidence interval[CI],0.75-0.92;P=3.95×10^(-4)).C1GALT1 mRNA expression levels were significantly higher in gastric tumor tissues than in normal tissues,and gastric cancer patients with higher C1GALT1 mRNA levels had worse overall survival rates(hazards ratio,1.33;95%CI,1.05-1.68;P_(log-rank)=1.90×10^(-2)).Furthermore,we found that C1GALT1 copy number differed in various immune cells and that C1GALT1 mRNA expression levels were positively correlated with the infiltrating levels of CD4^(+)T cells and *** results suggest that genetic variants of C1GALT1 may play an important role in gastric cancer risk and provide a new insight for C1GALT1 into a promising predictor of gastric cancer susceptibility and immune status.

关键词： o-glycosylation genetic variants immune status gastric cancer